The synthesis of some deoxygenated analogues of early intermediates in the biosynthesis of glycosylphosphatidylinositol (GPI) membrane anchors |
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| Authors: | Dix Alexander P Borissow Charles N Ferguson Michael A J Brimacombe John S |
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| Institution: | a School of Life Sciences (Chemistry), Carnelley Building, University of Dundee, Dundee DD1 4HN, UK
b School of Life Sciences (Biochemistry), Wellcome Trust Building, University of Dundee, Dundee DD1 5EH, UK |
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| Abstract: | Syntheses are described of 2-azido-4,6-di-O-benzyl-2,3-dideoxy-d-ribo-hexopyranosyl fluoride, 6-O-acetyl-2-azido-3-O-benzyl-2,4-dideoxy-d-xylo-hexopyranosyl fluoride and 2-azido-3,4-di-O-benzyl-2,6-dideoxy-d-glucopyranosyl fluoride. These glycosyl donors were coupled with the acceptor 1d-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-myo-inositol and the α-coupled products were transformed into α-d-3dGlcpN-PI, α-d-4dGlcpN-PI and α-d-6dGlcpN-PI by way of the H-phosphonate route. Brief mention is made of the biological evaluation of these deoxy-sugar analogues and their N-acetylated forms as candidate substrate/inhibitors of the N-deacetylase and α-(1→4)-d-mannosyltransferase activities present in trypanosomal and HeLa (human) cell-free system. |
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| Keywords: | Glycosylphosphatidylinositol (GPI) membrane anchors d-6-O-(2-amino-2-deoxy-α-d-glucopyranosyl)-myo-inositol 1-(1" target="_blank">Deoxy-sugar analogues of 1-d-6-O-(2-amino-2-deoxy-α-d-glucopyranosyl)-myo-inositol 1-(1 2-di-O-hexadecanoyl-sn-glycerol 3-phosphate) GPI biosynthesis in Trypanosoma brucei and HeLa (human) cell-free systems |
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